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This article begins with an awareness of two. One is to consider the meaning of “letter” sensibility, as expressed in Yi Sang’s text in relation to newspapers and printed media, which constituted modern media in the city of Gyeong-seong[京城] in the 1930’s. The other is to analyze Yi Sang’s dream of writing and of realizing his goals through the letter expression. Therefore, the objective of this article is to investigate the unique ideas about letters and the meaning of the expressions in the literary texts of Yi Sang, who omnidirectionally participated in the so-called “modernity of media,” as he drew figures, blueprints, and illustrations and worked as a magazine editor and literary coterie within modern Korean literature in the 1930’s. On the basis of this investigation, we tried to clarify the patterns in Yi Sang’s dreams of writing. Yi Sang’s unique ideas about letters were incorporated into his works in various forms and expressed through his original literary language. Moreover, his ideas had a sociocultural impact at that time beyond the function of delivering literary meanings. In his essay, “Lingering Impressions of a Mountain Village,” he expressed the natural mood that sprang up from rural society by replacing with metaphoric language acquired fromand sensitized by “urban emotions.” Hence, various aspects of Yi Sang’s literature constituting the so-called “rhetoric of city” were patterned by reflecting urban phenomena in visual forms in many parts of his works. The metaphoric system of the “rhetoric of city” established the unique metaphor in the viewpoint of the new modernity by the emotions and senses of those living in a city in the 20th century, saying good-bye to the senses of the 19th century. The characteristic elements of Yi Sang’s literature in the area of Korean literature in the 1930’s, which resulted from various forms of letters and their application to literary works, can ultimately be considered ventriloquial reactions to the speed of the capitalistic society that was changing rapidly, as well as to the disturbance of time and the entanglement of space in the changing process. This is a key factor in Yi Sang’s literature as well as the novel writing pattern that advocated the autonomy of art as “objectless writing’” based on the letter sensibility and the sign game method. Moreover, the new form of literature realized by Yi Sang’s letter sensibility and his literary world still requires an interpretation from a novel point of view, in the sense that it was an abstract painting that expressed the uneven consciousness of those living in a city, generated from the regulatory system of capitalistic reason that was rapidly expanding in the urban space of Gyeong-seong in the 1930’s.